How To Twenty Something teaches young professionals how to “adult” across various aspects of their lives from career, to relationships, to overall health and wellness, so they can gain the confidence to take risks and try new things, helping them to reach their full potential.
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Sep 28, 2026 · 15:10
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI Episode Summary If you're…
Sep 21, 2026 · 17:40
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI Episode Summary You don't…
Sep 14, 2026 · 15:31
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI Episode Summary What does…
Sep 7, 2026 · 17:13
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI Summary We spend so much of…
Aug 31, 2026 · 57:04
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI Episode Summary What if the…
Aug 24, 2026 · 20:13
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI Networking doesn't have to…
Aug 17, 2026 · 16:27
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI We spend so much time…
Aug 10, 2026 · 21:51
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI Your relationship to your…
Aug 3, 2026 · 16:50
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI Episode Summary How do you…
Jul 27, 2026 · 18:47
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI Episode Summary Have you…
Jul 20, 2026 · 1:00:27
Claim your free Human Design Chart before you listen: https://bit.ly/HD101-AC WATCH MY TEDX TALK: https://www.youtube.com/watch?v=RE_7I6vDKrI Human design is the ultimate…
Jul 13, 2026 · 18:17
WATCH MY TEDX TALK: https://www.youtube.com/watch?v=RE_7I6vDKrI NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ If you have ever felt like…
Jul 6, 2026 · 16:35
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ The job market is tough right now and I'm not going to sugarcoat it. In this episode I'm…
Jun 29, 2026 · 15:57
WATCH MY TEDX TALK: https://www.youtube.com/watch?v=RE_7I6vDKrI How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ If your twenties have felt confusing,…
Jun 22, 2026 · 18:53
NEW COURSE: How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ Watch my TEDx Talk: https://www.youtube.com/watch?v=RE_7I6vDKrI In this episode I am…
Jun 15, 2026 · 13:11
WATCH MY TEDX TALK: https://www.youtube.com/watch?v=RE_7I6vDKrI How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ If you've ever let a tiny oopsy consume…
Jun 8, 2026 · 16:54
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ This episode discusses something that's a lot harder to figure out than it sounds: knowing whether…
Jun 1, 2026 · 13:14
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ This episode is all about what to do when life decides to life… and by that I mean everything falls…
May 25, 2026 · 12:16
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ In this episode, I'm talking about the low that follows a really big high… that "now what?" feeling…
May 18, 2026 · 13:37
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ This episode breaks down the problem with always needing to accomplish things and why getting…
May 11, 2026 · 20:57
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ TRIGGER WARNING: Discussion of bodies, eating disorders, and skinniness, listen at your own discretion.…
May 4, 2026 · 56:04
How to Make Adulting Suck-Less: https://jessdiamondcoaching.com/suck-less/ Let’s face it, we’re not immortal.. There will come a day when we die. Which means it’s time to have…
Apr 27, 2026 · 20:21
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ In this special 150th episode, I’m reflecting on everything I got wrong in my twenties — from my career…
Apr 20, 2026 · 16:53
How to Make Adulting Suck Less: https://jessdiamondcoaching.com/suck-less/ This episode is all about your money story : the beliefs you developed about money growing up… and how…
Apr 13, 2026 · 19:39
Being self-employed isn’t as glamorous as social media makes it out to be. We’re talking numbers, emotions, expectations, timelines, doubts, and the grit that comes with this…
Apr 6, 2026 · 13:33
Feeling out of place is a normal part of your twenties. From identity shifts, to unexpected setbacks, to returning home, and the quiet disorientation that comes with becoming a…
Mar 30, 2026 · 54:57
Welcome all overthinkers! This episode talks about how improv translates into the real world by inviting you to play, be silly, and create a non-judgemental space.. All of which…
Mar 23, 2026 · 21:17
This episode breaks down the 10 sneaky red flags to watch out for in your relationship. Not the obvious things like cheating or abuse, but the quiet ones that don’t seem like a…
Mar 16, 2026 · 14:56
There’s no one “right” answer when it comes to how far you should live from work, there’s only the choice that best supports the life you’re trying to build right now. This…
Mar 9, 2026 · 12:29
In this birthday episode, I’m reflecting on my last year in my twenties and why, despite everything I’ve been through, life really is getting easier. Not because life stops…
Mar 2, 2026 · 18:44
This episode breaks down the coping mechanisms most twenty-somethings use when life feels overwhelming and what those habits actually say about you. I run you through the top 10…
Feb 23, 2026 · 14:56
This episode breaks down the quick fixes we’re constantly being sold and why they don’t actually work when it comes to obtaining results. I explain why these tactics feel…
Feb 16, 2026 · 16:26
You are nothing without a routine! This episode is all about building one up from scratch so you create one that’s actually going to work for you. From nighttime and morning…
Feb 9, 2026 · 15:14
If you’ve communicated clearly, calmly, and more than once, and nothing has changed, this episode is for you. It isn’t about learning how to communicate better in the moment;…
Feb 2, 2026 · 15:10
This episode breaks down why being picky is not a bad thing and how this doesn’t only apply to dating. The truth is your friendships, career, and relationship with yourself all…
Jan 26, 2026 · 16:39
This episode breaks down why we all fear wasting our twenties. The pressure to travel, date, go out every weekend, and have life “figured out” can make it feel like one wrong…
Jan 19, 2026 · 14:20
In this episode, I’m breaking down one of the biggest money myths twenty-somethings fall for: the idea that more money will magically fix your financial stress. The truth is that…
Jan 12, 2026 · 16:25
This episode is for you if you’re facing a season of discontent. Whether it’s career dissatisfaction, friendship shifts, relationship anxiety, and even how the city you live in…
Jan 5, 2026 · 17:09
This episode guides you through a real rewind and reflection of my 2025 — the wins, the hard stuff, and how I’m using both to set more intentional goals for 2026. I share some of…
Dec 29, 2025 · 16:14
What happens when nothing sounds like a good idea and you feel completely stuck in your life? This episode talks about how we usually end up in one of two places: the Land of No…
Dec 22, 2025 · 15:15
If you’re always tired, you’re not alone, but you also might be the reason for your exhaustion. From shorter days and less sunlight to sitting for 10 hours straight, I explain…
Dec 15, 2025 · 17:37
In this episode, I’m walking you through everything you need to know to prep for your next interview: what to do before, during, and after. I share how to make a strong first…
Dec 8, 2025 · 55:30
Networking… something we all know we need to do, yet are so turned off by the idea of small talk and dead end connections. Which is why it’s time for you to learn how to network,…
Dec 1, 2025 · 14:37
If you’ve ever called yourself lazy or felt guilty for not having the energy to keep up with your “good habits,” this episode is for you. Laziness gets a bad rap, but what if…
Nov 24, 2025 · 15:01
Show notes If you’ve ever caught yourself spiraling about outcomes that don’t even exist yet, you’re not alone. We all want answers before they’re ready to come, but that need…
Nov 17, 2025 · 17:20
In this episode, I talk about the fine line between being selfish in a healthy way… the kind that protects your energy and honors your needs and the kind that starts to isolate…
Nov 10, 2025 · 55:58
How do you know if the person you’re with is your forever person? This episode dives into what to look for in your relationship and ends with the number one question you should…
Nov 3, 2025 · 17:18
Friendship in your twenties is messy, complicated, and always changing. In this episode, I’m breaking down what it actually means to be a good friend and how to avoid falling…
Oct 27, 2025 · 16:16
No one warns you about the different types of loss that comes with growing up. It’s not all bad, but it is bittersweet. You lose old versions of yourself, friendships that don’t…
Oct 20, 2025 · 15:49
Your twenties are basically one big pivot, so let’s talk about how to handle them without losing your mind. From careers to relationships to moving cities to changing habits,…
Oct 13, 2025 · 17:08
In this episode, I’m breaking down one of the biggest living decisions you face in your twenties: should you live with roommates or live alone? I share stories from my own…
Oct 6, 2025 · 13:26
In this episode, I’m diving into the big question we all ask at some point: what’s the point? Whether it’s about college, your 9–5 job, dating, or just life in general, it’s…
Sep 29, 2025 · 17:33
In this episode, I’m diving into all the things no one really tells you about being an adult. I share the story of my very first “oh crap, I’m an adult” moment and how that…
Sep 22, 2025 · 19:39
This episode talks about the gut-punch feeling of “everyone is hanging out without me,” why it hits so hard in your twenties, and how to tell the difference between being…
Sep 15, 2025 · 21:53
In this episode, I’m breaking down what it feels like to be in the in between —that frustrating, uncomfortable space where you're actively working toward your next thing but not…
Sep 8, 2025 · 58:15
No, this is not your typical ‘love yourself’ kind of episode, but rather getting into the real thoughts and real emotions behind being single – the good and the bad. Danielle…
Sep 1, 2025 · 19:17
If I had to land a full-time job in today’s market, here are the exact five steps I’d take. In this episode, I’m sharing the strategies I wish I knew back when I was mass…
Aug 25, 2025 · 57:26
Moving in together is a big next step for a relationship and there are so many conversations that need to be shared prior to making this decision and progressing your…
Aug 18, 2025 · 18:27
After spending a week at Experience Camps in Georgia, I’m more convinced than ever that every adult needs to go to camp . In this episode, I reflect on what it meant to step away…
Aug 11, 2025 · 1:01:34
Everything you know about nutrition is wrong! That’s why I brought on Dee Jackson to help me discuss common nutrition statements and break down the truth and the falseness behind…
Aug 4, 2025 · 17:05
Show notes Your twenties can feel like one giant WTF moment—and in this episode, I unpack why that is and what to actually do about it. Throughout this episode I share my own…
Jul 28, 2025 · 58:52
In a heavily masculine dominated world (the patriarchy), it can be really difficult for people to shift into their feminine side. The truth? We need both to create relationships…
Jul 21, 2025 · 20:43
In this episode, I’m diving back into the fitness world and calling out five major myths that so many of us fall for. Whether you’re a seasoned gym-goer or someone just starting…
Jul 14, 2025 · 53:37
What are your red light, yellow light, green light moments in your friendships? This episode highlights behaviors that signify a good friendship from a bad one, how you can use…
Jul 7, 2025 · 16:22
Jealousy is one of those emotions we all experience but rarely talk about—especially in our twenties when comparison is everywhere and progress feels like a race with no clear…
Jun 30, 2025 · 54:32
You’ve heard the saying, “make your money work for you,” but that can mean so many different things. Author of More Than Cash, Julia Cancro, introduces the easiest ways to invest…
Jun 23, 2025 · 19:37
Whether you're super close with them, feel distant, or have complicated dynamics, your relationship to your parents is something most of us are quietly navigating. In this…
Jun 16, 2025 · 53:23
Time is a funny concept. We all measure it differently based on what we’re going through and what we’re seeing around us. Lou Smith went from professional basketball player to…
Jun 9, 2025 · 15:53
Whether you’ve been ghosted, done the ghosting (yep, I see you), or just hate how common it’s become, this episode is for you. I’m calling ghosting out for what it really is—a…
Jun 2, 2025 · 55:17
We all want to make money.. It’s how we’ll be able to live our lives, travel the world, create experiences, but knowing how to ask for more money requires thought, preparation,…
May 26, 2025 · 18:38
In this episode, I’m challenging the age-old idea that “quitters never win.” Sometimes, quitting is the bravest and wisest choice you can make—and that’s exactly what I unpack in…
May 19, 2025 · 56:26
If you are not happy with where you’re working, toxic or not, you need to get out! This episode brought on Career and Executive Coach, Dr. Kristy Taylor, to break down what you…
May 12, 2025 · 22:59
Happy 100th Episode of How To Twenty-Something!!! This episode is a full-on celebration, a reflection, and honestly, a love letter to being yourself. I’m talking about what it…
May 5, 2025 · 57:28
People always say, ‘You’re young, take the risk,’ but what they don’t talk about is what that looks like, how you can do so, and why your twenties are THE time to take a risk in…
Apr 28, 2025 · 24:40
This is NOT Your Life on 4/29: https://jessdiamondcoaching.com/noise/ Procrastination isn’t just about laziness—it’s often rooted in fear of failure, perfectionism, or avoiding…
Apr 21, 2025 · 56:51
Living a life that you are proud of and happy with means living a life that is built on your own terms. We all have different views of the world and those views help us take…
Apr 14, 2025 · 24:19
This is NOT Your Life on 4/29: https://jessdiamondcoaching.com/noise/ This episode dives into the differences between organic and online dating, exploring how mindset,…
Apr 7, 2025 · 57:57
I know you probably know what LinkedIN is, but are you optimizing it’s existence to your advantage? Social Media Manager, Katie McKiever, is the guest for this episode where she…
Mar 31, 2025 · 20:10
Moving to a new city is scary, but it doesn’t have to be. This episode dives into the challenges and excitement of moving to a new city in your twenties. I offer practical advice…
Mar 24, 2025 · 49:17
How do you break down who you are in a world that is constantly trying to define you? Aaron Gordon is a twin and took over his family business, so he knows exactly what it means…
Mar 17, 2025 · 24:13
In this episode of How to Twenty-Something , I’m diving into the power of non-negotiables—those personal standards that shape your decisions, relationships, career, and daily…
Mar 10, 2025 · 53:09
Being brave does not mean you are without fear, in fact it means you are filled with fear but you are able to take action despite it. This episode of How To Twenty-Something…
Mar 3, 2025 · 25:14
Developing confidence is definitely one of those things that feels intangible or hard to come by. But here’s a secret: the most confident person you know also had to build this…
Feb 24, 2025 · 55:04
TRIGGER WARNING: mention of assault, rape, and abuse in this episode National Domestic Violence Hotline: 800-799-7233 or text BEGIN to 88788 21 Days to Unbreakable is a 21-day…
Feb 17, 2025 · 19:43
No matter how hard we try, rejection is unavoidable—it shows up in our personal lives, careers, friendships, and even the unexpected moments. In this episode, I share my own…
Feb 10, 2025 · 49:27
SELF REFLECTION! SELF REFLECTION! SELF REFLECTION! That is the theme of this episode when it comes to building up your own personal brand. This episode talks about what you need…
Feb 3, 2025 · 20:53
In this episode, I share my journey of leaving the corporate world to become self-employed at 25 and how I’ve helped other twenty-somethings do the same. I talk about the year…
Jan 27, 2025 · 53:03
Have you ever thought about leaving your belongings and life behind to become a travel nomad? I know I have and this episode of How To Twenty-Something brings on Liz Erhartic to…
Jan 20, 2025 · 19:32
Despite living in a world designed for connection, many of us feel more isolated than we ever imagined, especially during a decade full of transitions. In this episode, I share…
Jan 13, 2025 · 51:28
From door to door sales, to logistics and cold calling, to advertisement, to procurement analyst, to taking a 3 month hiatus in Alaska, Orien has had quite the career path and is…
Jan 6, 2025 · 18:03
Your career impacts every aspect of your life, and it’s crucial to make moves that align with your values while embracing the flexibility and risks unique to your twenties. This…
Dec 30, 2024 · 59:20
What you believe to be true, will become the truth for you. This episode of How To Twenty-Something invites on High Performance Coach, Corinne Eckert, to discuss how your…
Dec 23, 2024 · 19:40
In this episode of How to Twenty-Something, I explore the importance of becoming decisive and how it can transform your twenties. I share practical tips, like starting with…
Dec 16, 2024 · 46:53
There are so many changes and transitions that happen in your twenties, most of which take a toll on your mental health. So this episode invites Dr. Lauren Chase to discuss…
Dec 9, 2024 · 19:19
In this episode of How to Twenty-Something , I dive into the realities of being single at weddings. As someone who’s often flown solo to weddings, I get into the highs and lows…
Dec 2, 2024 · 50:09
Do you find yourself trapped in your relationships or constantly attracting the ‘wrong’ person to your life? Well this episode of How To Twenty-Something breaks down your…
Nov 25, 2024 · 19:51
This episode of How To Twenty-Something talks about the complex world of imposter syndrome—how it shows up in our careers, relationships, and daily lives, especially in our…
Nov 18, 2024 · 1:06:01
This episode of How To Twenty-Something talks about why it’s good to add weight to the bar when you’re in the gym and muscle to your body. Jake Packett and I debunk common fears…
Nov 11, 2024 · 23:18
This episode of How To Twenty-Something encompasses the root causes of burnout and its impact on different aspects of life—whether it’s careers, relationships, health, or the…
Nov 4, 2024 · 51:03
Having reciprocity in your relationships means you are showing up and pouring yourself into another person while also receiving the same in return; it’s reaching an equilibrium.…
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